5-Bromo-1,2,3-trimethoxybenzene → HCID 178418846, compound

Participants

Reaction Steps

To a stirred solution of n-butyllithium (3.7 mL, 1.6 M in hexane solution, 6.0 mmol) in dry ether (40 mL), a solution of 3,4,5-trimethoxyphenylbromide (0.74 g, 3.0 mmol) in ether (20 mL) was added under dry nitrogen at −78° C. The solution was stirred for 1 h in order to form 3,4,5-trimethoxyphenyllithum. The ketone reagent (3.0 mmol) was added at −20° C., and the stirring was continued for 2 h (−20° C.-rt). The mixture was partitioned between CH2Cl2 and water, the organic layer was dried over anhydrous sodium sulfate, and, after filtration, the organic layer was concentrated in vacuo to provide a yellow oil. The compound was purified by column chromatography.

Provenance & Evidence